Bis[μ-(E)-N′-(4-oxido-4-phenyl­but-3-en-2-yl­idene)benzohydrazidato]bis­[pyridine­copper(II)]

Hatefi, M.; Sheikhshoaie, I.; Moghadam, M.; Mirkhani, V.; Kia, R.

doi:10.1107/S1600536810019902

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m726-m727

doi:10.1107/S1600536810019902

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Bis[μ-(E)-N′-(4-oxido-4-phenylbut-3-en-2-ylidene)benzohydrazidato]bis[pyridinecopper(II)]

Mehdi Hatefi,^a Iran Sheikhshoaie,^a ^* Majid Moghadam,^b Valiollah Mirkhani ^b and Reza Kia ^c,^d ‡

^aChemistry Department, Shahid Bahonar University, Kerman, Iran, ^bDepartment of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^dX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: i_shoaie@yahoo.com

(Received 16 May 2010; accepted 26 May 2010; online 5 June 2010)

In the crystal structure of the title centrosymmetric dimer, [Cu₂(C₁₇H₁₄N₂O₂)₂(C₅H₅N)₂], the Cu^II atom has an almost perfect square-pyramidal geometry. The Cu^II ion is coordinated by the NO₂ donor atoms of the hydrazide Schiff base ligand, the N atom of the pyridine group and an O atom of the symmetry-related unit. The dihedral angles between the pyridine ring and the two phenyl rings of the ligand are 21.4 (3) and 24.0 (2)°. The molecular structure is stabilized by intramolecular C—H⋯O interactions.

Related literature

For background to the properties of hydrazide Schiff base–metal complexes, see: Rao et al. (1990 ); West et al. (1993 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Cu₂(C₁₇H₁₄N₂O₂)₂(C₅H₅N)₂]
M_r = 841.88
Monoclinic, P 2₁ /c
a = 9.2678 (19) Å
b = 20.903 (4) Å
c = 11.907 (4) Å
β = 122.65 (2)°
V = 1942.2 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 296 K
0.25 × 0.19 × 0.08 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995 ; Spek, 2009 ) T_min = 0.791, T_max = 1.179
22473 measured reflections
3419 independent reflections
2396 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.091
S = 0.98
3419 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O1	0.93	2.34	2.892 (6)	117
C22—H22A⋯O2	0.93	2.37	2.940 (5)	119

Data collection: X-AREA (Stoe & Cie, 2007 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019902/su2179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810019902/su2179Isup2.hkl

checkCIF report

Comment top

Among ligand systems hydrazines and hydrazones occupy a special place because the transition metal complexes of these ligands, developed due to their chelating capacity and structural flexibility, have interesting electrical as well as magnetic properties (Rao et al., 1990), and pharmacological activities, such as antibacterial, antitumoural, antiviral antimalaria, antituberculosis (West et al., 1993).

The molecular structure of the title molecule is illustrated in Fig. I. It is a novel hydrazido-Schiff base copper(II) complex, with the Cu^II atom having a N2O2 square-pyramidal geometry. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The dihedral angles between the pyridine ring (N3/C18-C22) and the phenyl rings, A (C1-C6) and B (C12-C17), of the ligand are 21.4 (3) and 24.0 (2)°, respectively. The molecular structure is stabilized by intramolecular C—H···O interactions (Fig. 2, Table 1).

In the crystal the molecules are held together by normal van der Waals interactions (Fig. 3).

Related literature top

For background to the properties of hydrazide Schiff base–metal complexes, see: Rao et al. (1990); West et al. (1993). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by adding (E)-N'- (4-oxo-4-phenyl butane-2-ylidene) benzohydrazide (1 mmol) to a solution of Cu(OAc)₂. H₂O (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 30 min. It was then placed under a fume hood, near to the a solution of another sample which had pyridine as solvent of crystallization. As a consequence pyridine diffused into the methanol solution and resulted in the formation of brown single crystals of the title complex, over several days.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2007); cell refinement: X-AREA (Stoe & Cie, 2007); data reduction: X-RED (Stoe & Cie, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title complex, showing 40% probability displacement ellipsoids (H-toms have been omitted for clarity).
	Fig. 2. The asymmetric unit of the title compound. The dashed lines show the intramolecular C-H···O interactions.
	Fig. 3. The crystal packing of the title compound, viewed down the b-axis.

Bis[µ-(E)-N'-(4-oxido-4-phenylbut-3-en-2- ylidene)benzohydrazidato]bis[pyridinecopper(II)] top

Crystal data top

[Cu₂(C₁₇H₁₄N₂O₂)₂(C₅H₅N)₂]	F(000) = 868
M_r = 841.88	D_x = 1.440 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2500 reflections
a = 9.2678 (19) Å	θ = 2.3–27.8°
b = 20.903 (4) Å	µ = 1.15 mm⁻¹
c = 11.907 (4) Å	T = 296 K
β = 122.65 (2)°	Block, brown
V = 1942.2 (8) Å³	0.25 × 0.19 × 0.08 mm
Z = 2

Data collection top

Stoe IPDS II diffractometer	3419 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995; Spek, 2009)	h = −11→11
T_min = 0.791, T_max = 1.179	k = −24→23
22473 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0421P)²] where P = (F_o² + 2F_c²)/3
3419 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Cu₂(C₁₇H₁₄N₂O₂)₂(C₅H₅N)₂]	V = 1942.2 (8) Å³
M_r = 841.88	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2678 (19) Å	µ = 1.15 mm⁻¹
b = 20.903 (4) Å	T = 296 K
c = 11.907 (4) Å	0.25 × 0.19 × 0.08 mm
β = 122.65 (2)°

Data collection top

Stoe IPDS II diffractometer	3419 independent reflections
Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995; Spek, 2009)	2396 reflections with I > 2σ(I)
T_min = 0.791, T_max = 1.179	R_int = 0.086
22473 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 0.98	Δρ_max = 0.60 e Å⁻³
3419 reflections	Δρ_min = −0.24 e Å⁻³
248 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.72076 (6)	0.989490 (19)	0.59789 (4)	0.03829 (14)
O1	0.8469 (3)	0.91348 (12)	0.6768 (2)	0.0487 (6)
O2	0.5995 (3)	1.06734 (11)	0.5062 (2)	0.0483 (7)
N1	0.7488 (4)	0.98572 (15)	0.4481 (3)	0.0472 (5)
N2	0.6903 (4)	1.04093 (15)	0.3654 (3)	0.0472 (5)
N3	0.7158 (4)	1.01066 (15)	0.7612 (3)	0.0414 (7)
C1	1.0439 (5)	0.8085 (2)	0.8269 (4)	0.0516 (10)
H1A	1.0469	0.8445	0.8738	0.062*
C2	1.1150 (5)	0.7523 (2)	0.8941 (4)	0.0604 (12)
H2A	1.1679	0.7510	0.9862	0.073*
C3	1.1088 (6)	0.6981 (2)	0.8270 (5)	0.0641 (12)
H3A	1.1566	0.6601	0.8730	0.077*
C4	1.0307 (6)	0.7005 (2)	0.6901 (5)	0.0635 (12)
H4A	1.0251	0.6637	0.6438	0.076*
C5	0.9611 (5)	0.75679 (18)	0.6218 (4)	0.0517 (10)
H5A	0.9094	0.7580	0.5297	0.062*
C6	0.9678 (4)	0.81204 (17)	0.6902 (4)	0.0404 (9)
C7	0.8931 (5)	0.87399 (17)	0.6172 (4)	0.0435 (9)
C8	0.8818 (5)	0.88587 (18)	0.5004 (4)	0.0486 (10)
H8A	0.9209	0.8535	0.4696	0.058*
C9	0.8162 (5)	0.94287 (19)	0.4177 (4)	0.0509 (10)
C10	0.8303 (6)	0.9466 (2)	0.2981 (4)	0.0630 (12)
H10A	0.8992	0.9829	0.3068	0.095*
H10B	0.7180	0.9512	0.2190	0.095*
H10C	0.8826	0.9082	0.2921	0.095*
C11	0.6189 (4)	1.07952 (16)	0.4061 (3)	0.0377 (8)
C12	0.5563 (4)	1.14232 (16)	0.3377 (3)	0.0390 (8)
C13	0.5943 (5)	1.16228 (19)	0.2453 (4)	0.0555 (11)
H13A	0.6581	1.1360	0.2249	0.067*
C14	0.5383 (6)	1.2207 (2)	0.1837 (5)	0.0695 (13)
H14A	0.5662	1.2338	0.1231	0.083*
C15	0.4425 (6)	1.2595 (2)	0.2104 (5)	0.0663 (13)
H15A	0.4033	1.2985	0.1669	0.080*
C16	0.4035 (5)	1.2407 (2)	0.3021 (5)	0.0625 (12)
H16A	0.3388	1.2673	0.3211	0.075*
C17	0.4606 (5)	1.18260 (17)	0.3654 (4)	0.0476 (10)
H17A	0.4347	1.1702	0.4276	0.057*
C18	0.7643 (6)	0.96766 (19)	0.8587 (4)	0.0561 (11)
H18A	0.7996	0.9274	0.8495	0.067*
C19	0.7642 (7)	0.9806 (3)	0.9721 (4)	0.0797 (15)
H19A	0.8004	0.9498	1.0385	0.096*
C20	0.7102 (7)	1.0389 (2)	0.9855 (5)	0.0814 (16)
H20A	0.7094	1.0486	1.0614	0.098*
C21	0.6573 (6)	1.0830 (2)	0.8863 (4)	0.0700 (13)
H21A	0.6188	1.1230	0.8931	0.084*
C22	0.6618 (5)	1.06729 (19)	0.7760 (4)	0.0514 (10)
H22A	0.6256	1.0976	0.7087	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0494 (3)	0.0364 (2)	0.0337 (2)	−0.0004 (2)	0.02546 (19)	0.0017 (2)
O1	0.0575 (17)	0.0441 (15)	0.0517 (16)	0.0063 (13)	0.0342 (14)	0.0053 (12)
O2	0.0690 (18)	0.0422 (15)	0.0389 (15)	−0.0001 (13)	0.0324 (14)	0.0067 (11)
N1	0.0515 (13)	0.0442 (12)	0.0462 (13)	0.0004 (11)	0.0266 (12)	0.0062 (10)
N2	0.0515 (13)	0.0442 (12)	0.0462 (13)	0.0004 (11)	0.0266 (12)	0.0062 (10)
N3	0.0501 (17)	0.0420 (17)	0.0330 (15)	−0.0047 (15)	0.0231 (14)	−0.0017 (15)
C1	0.049 (2)	0.059 (3)	0.049 (2)	0.010 (2)	0.028 (2)	0.007 (2)
C2	0.057 (3)	0.079 (3)	0.047 (2)	0.015 (2)	0.029 (2)	0.021 (2)
C3	0.058 (3)	0.059 (3)	0.072 (3)	0.014 (2)	0.033 (3)	0.029 (3)
C4	0.064 (3)	0.045 (3)	0.077 (3)	0.009 (2)	0.035 (3)	0.003 (2)
C5	0.056 (3)	0.049 (3)	0.048 (2)	0.008 (2)	0.027 (2)	0.007 (2)
C6	0.034 (2)	0.044 (2)	0.044 (2)	0.0040 (17)	0.0213 (18)	0.0074 (17)
C7	0.038 (2)	0.041 (2)	0.052 (2)	−0.0006 (17)	0.0237 (19)	−0.0020 (18)
C8	0.059 (3)	0.039 (2)	0.047 (2)	0.0087 (19)	0.028 (2)	0.0037 (18)
C9	0.056 (3)	0.061 (3)	0.047 (2)	−0.007 (2)	0.036 (2)	−0.008 (2)
C10	0.087 (3)	0.064 (3)	0.058 (3)	0.016 (2)	0.053 (3)	0.012 (2)
C11	0.038 (2)	0.035 (2)	0.0330 (19)	−0.0079 (16)	0.0148 (17)	−0.0002 (15)
C12	0.040 (2)	0.036 (2)	0.0319 (19)	−0.0064 (16)	0.0139 (17)	0.0040 (16)
C13	0.068 (3)	0.054 (3)	0.054 (3)	0.005 (2)	0.039 (2)	0.014 (2)
C14	0.081 (3)	0.066 (3)	0.068 (3)	0.001 (3)	0.044 (3)	0.031 (2)
C15	0.056 (3)	0.047 (3)	0.074 (3)	0.001 (2)	0.020 (3)	0.022 (2)
C16	0.054 (3)	0.045 (3)	0.087 (3)	0.004 (2)	0.036 (3)	0.002 (2)
C17	0.051 (2)	0.043 (2)	0.051 (2)	−0.0061 (19)	0.029 (2)	0.0037 (18)
C18	0.080 (3)	0.049 (2)	0.045 (2)	0.004 (2)	0.038 (2)	0.0058 (18)
C19	0.126 (4)	0.078 (3)	0.051 (3)	0.012 (3)	0.058 (3)	0.013 (3)
C20	0.127 (5)	0.082 (3)	0.052 (3)	0.007 (3)	0.059 (3)	−0.002 (3)
C21	0.102 (4)	0.058 (3)	0.058 (3)	0.006 (3)	0.048 (3)	−0.009 (2)
C22	0.072 (3)	0.041 (2)	0.046 (2)	−0.003 (2)	0.034 (2)	−0.0011 (18)

Geometric parameters (Å, º) top

Cu1—O1	1.894 (2)	C9—C10	1.500 (5)
Cu1—N1	1.938 (3)	C10—H10A	0.9600
Cu1—O2	1.944 (2)	C10—H10B	0.9600
Cu1—N3	2.018 (3)	C10—H10C	0.9600
O1—C7	1.301 (4)	C11—C12	1.488 (5)
O2—C11	1.323 (4)	C12—C17	1.385 (5)
N1—C9	1.252 (5)	C12—C13	1.389 (5)
N1—N2	1.421 (4)	C13—C14	1.373 (6)
N2—C11	1.292 (4)	C13—H13A	0.9300
N3—C22	1.333 (5)	C14—C15	1.361 (6)
N3—C18	1.340 (4)	C14—H14A	0.9300
C1—C2	1.372 (5)	C15—C16	1.379 (6)
C1—C6	1.383 (5)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.376 (5)
C2—C3	1.370 (6)	C16—H16A	0.9300
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.381 (6)	C18—C19	1.377 (6)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.378 (5)	C19—C20	1.359 (6)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.395 (5)	C20—C21	1.365 (6)
C5—H5A	0.9300	C20—H20A	0.9300
C6—C7	1.504 (5)	C21—C22	1.376 (5)
C7—C8	1.361 (5)	C21—H21A	0.9300
C8—C9	1.453 (5)	C22—H22A	0.9300
C8—H8A	0.9300

O1—Cu1—N1	93.94 (12)	C9—C10—H10A	109.5
O1—Cu1—O2	174.68 (10)	C9—C10—H10B	109.5
N1—Cu1—O2	80.87 (12)	H10A—C10—H10B	109.5
O1—Cu1—N3	92.01 (12)	C9—C10—H10C	109.5
N1—Cu1—N3	168.38 (13)	H10A—C10—H10C	109.5
O2—Cu1—N3	92.90 (11)	H10B—C10—H10C	109.5
C7—O1—Cu1	123.9 (2)	N2—C11—O2	124.3 (3)
C11—O2—Cu1	110.4 (2)	N2—C11—C12	118.2 (3)
C9—N1—N2	116.4 (3)	O2—C11—C12	117.4 (3)
C9—N1—Cu1	129.1 (3)	C17—C12—C13	118.3 (3)
N2—N1—Cu1	114.5 (2)	C17—C12—C11	121.1 (3)
C11—N2—N1	109.2 (3)	C13—C12—C11	120.6 (3)
C22—N3—C18	117.1 (3)	C14—C13—C12	120.4 (4)
C22—N3—Cu1	121.8 (2)	C14—C13—H13A	119.8
C18—N3—Cu1	121.1 (3)	C12—C13—H13A	119.8
C2—C1—C6	120.8 (4)	C15—C14—C13	120.8 (4)
C2—C1—H1A	119.6	C15—C14—H14A	119.6
C6—C1—H1A	119.6	C13—C14—H14A	119.6
C3—C2—C1	120.8 (4)	C14—C15—C16	119.9 (4)
C3—C2—H2A	119.6	C14—C15—H15A	120.1
C1—C2—H2A	119.6	C16—C15—H15A	120.1
C2—C3—C4	119.3 (4)	C17—C16—C15	119.8 (4)
C2—C3—H3A	120.4	C17—C16—H16A	120.1
C4—C3—H3A	120.4	C15—C16—H16A	120.1
C5—C4—C3	120.5 (4)	C16—C17—C12	120.9 (4)
C5—C4—H4A	119.7	C16—C17—H17A	119.6
C3—C4—H4A	119.7	C12—C17—H17A	119.6
C4—C5—C6	120.2 (4)	N3—C18—C19	122.7 (4)
C4—C5—H5A	119.9	N3—C18—H18A	118.6
C6—C5—H5A	119.9	C19—C18—H18A	118.6
C1—C6—C5	118.4 (3)	C20—C19—C18	119.1 (4)
C1—C6—C7	120.6 (3)	C20—C19—H19A	120.4
C5—C6—C7	120.9 (3)	C18—C19—H19A	120.4
O1—C7—C8	125.1 (3)	C19—C20—C21	119.1 (4)
O1—C7—C6	114.6 (3)	C19—C20—H20A	120.4
C8—C7—C6	120.3 (3)	C21—C20—H20A	120.4
C7—C8—C9	128.0 (3)	C20—C21—C22	118.9 (4)
C7—C8—H8A	116.0	C20—C21—H21A	120.5
C9—C8—H8A	116.0	C22—C21—H21A	120.5
N1—C9—C8	118.9 (3)	N3—C22—C21	123.0 (4)
N1—C9—C10	123.3 (4)	N3—C22—H22A	118.5
C8—C9—C10	117.8 (3)	C21—C22—H22A	118.5

N1—Cu1—O1—C7	−11.1 (3)	O1—C7—C8—C9	−0.8 (7)
N3—Cu1—O1—C7	178.8 (3)	C6—C7—C8—C9	−179.0 (4)
N1—Cu1—O2—C11	−7.6 (2)	N2—N1—C9—C8	178.7 (3)
N3—Cu1—O2—C11	162.6 (2)	Cu1—N1—C9—C8	1.6 (6)
O1—Cu1—N1—C9	5.3 (4)	N2—N1—C9—C10	−2.4 (6)
O2—Cu1—N1—C9	−175.9 (4)	Cu1—N1—C9—C10	−179.5 (3)
N3—Cu1—N1—C9	125.9 (6)	C7—C8—C9—N1	−5.9 (7)
O1—Cu1—N1—N2	−171.9 (2)	C7—C8—C9—C10	175.2 (4)
O2—Cu1—N1—N2	6.9 (2)	N1—N2—C11—O2	−2.3 (5)
N3—Cu1—N1—N2	−51.3 (7)	N1—N2—C11—C12	176.8 (3)
C9—N1—N2—C11	177.7 (3)	Cu1—O2—C11—N2	8.0 (4)
Cu1—N1—N2—C11	−4.7 (4)	Cu1—O2—C11—C12	−171.2 (2)
O1—Cu1—N3—C22	169.8 (3)	N2—C11—C12—C17	172.2 (3)
N1—Cu1—N3—C22	49.0 (8)	O2—C11—C12—C17	−8.7 (5)
O2—Cu1—N3—C22	−8.2 (3)	N2—C11—C12—C13	−8.5 (5)
O1—Cu1—N3—C18	−11.3 (3)	O2—C11—C12—C13	170.6 (3)
N1—Cu1—N3—C18	−132.1 (6)	C17—C12—C13—C14	0.2 (6)
O2—Cu1—N3—C18	170.7 (3)	C11—C12—C13—C14	−179.1 (4)
C6—C1—C2—C3	−1.5 (6)	C12—C13—C14—C15	−1.1 (7)
C1—C2—C3—C4	0.4 (7)	C13—C14—C15—C16	1.2 (7)
C2—C3—C4—C5	0.6 (7)	C14—C15—C16—C17	−0.5 (7)
C3—C4—C5—C6	−0.4 (6)	C15—C16—C17—C12	−0.4 (6)
C2—C1—C6—C5	1.7 (6)	C13—C12—C17—C16	0.5 (6)
C2—C1—C6—C7	−178.8 (4)	C11—C12—C17—C16	179.8 (3)
C4—C5—C6—C1	−0.7 (6)	C22—N3—C18—C19	−1.7 (6)
C4—C5—C6—C7	179.8 (4)	Cu1—N3—C18—C19	179.4 (4)
Cu1—O1—C7—C8	10.8 (5)	N3—C18—C19—C20	1.0 (8)
Cu1—O1—C7—C6	−170.9 (2)	C18—C19—C20—C21	0.2 (8)
C1—C6—C7—O1	−24.9 (5)	C19—C20—C21—C22	−0.7 (8)
C5—C6—C7—O1	154.6 (3)	C18—N3—C22—C21	1.1 (6)
C1—C6—C7—C8	153.5 (4)	Cu1—N3—C22—C21	−179.9 (3)
C5—C6—C7—C8	−27.0 (5)	C20—C21—C22—N3	0.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O1	0.93	2.34	2.892 (6)	117
C22—H22A···O2	0.93	2.37	2.940 (5)	119

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₇H₁₄N₂O₂)₂(C₅H₅N)₂]
M_r	841.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.2678 (19), 20.903 (4), 11.907 (4)
β (°)	122.65 (2)
V (Å³)	1942.2 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.25 × 0.19 × 0.08

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Multi-scan (MULABS in PLATON; Blessing, 1995; Spek, 2009)
T_min, T_max	0.791, 1.179
No. of measured, independent and observed [I > 2σ(I)] reflections	22473, 3419, 2396
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.091, 0.98
No. of reflections	3419
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.24

Computer programs: X-AREA (Stoe & Cie, 2007), X-RED (Stoe & Cie, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O1	0.93	2.34	2.892 (6)	117
C22—H22A···O2	0.93	2.37	2.940 (5)	119

Footnotes

‡Additional corresponding author: e-mail: rkia@srbiau.ac.ir; zsrkk@yahoo.com.

Acknowledgements

The support of this work by the Shahid Bahonar University of Kerman is acknowledged. RK thanks the Science and Research Branch, Islamic Azad University for support.

References

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